Ametamey, Simon M; Heimgartner, Heinz (1990). Umsetzung von 3-(Dimethylamino)-2H-azirinen mit 1,3-Oxazolidin-2-thion zu 3-(2-Hydroxyethyl)-2-thiohydantoinen. Helvetica Chimica Acta, 73(3):594-598.
The reaction of 3-(dimethylamino)-2H-azirines 1 and 1,3-oxazolidine-2-thione (6), in MeCN at room temperature, yields, after hydrolytic workup, 3-(2-hydroxyethyl)-2-thiohydantoins 7 (Scheme 2). In the case of the spirocyclic 1c , crystallization of the crude reaction mixture leads to spiro[cyclopentane-l,7'(7'aH)-imidazo[4.3-b]oxazole]-5'-thione 8c. The mechanism is discussed.
The reaction of 3-(dimethylamino)-2H-azirines 1 and 1,3-oxazolidine-2-thione (6), in MeCN at room temperature, yields, after hydrolytic workup, 3-(2-hydroxyethyl)-2-thiohydantoins 7 (Scheme 2). In the case of the spirocyclic 1c , crystallization of the crude reaction mixture leads to spiro[cyclopentane-l,7'(7'aH)-imidazo[4.3-b]oxazole]-5'-thione 8c. The mechanism is discussed.
| Other titles: | Reaction of 3-(Dimethylamino)-2H-azirines with 1,3-Oxazolidine-2-thione to 3-(2-Hydroxyethyl)-2-thiohydantoins |
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| Item Type: | Journal Article, refereed, original work |
| Communities & Collections: | 07 Faculty of Science > Department of Chemistry |
| Dewey Decimal Classification: | 540 Chemistry |
| Scopus Subject Areas: | Physical Sciences > Catalysis
Life Sciences > Biochemistry Life Sciences > Drug Discovery Physical Sciences > Physical and Theoretical Chemistry Physical Sciences > Organic Chemistry Physical Sciences > Inorganic Chemistry |
| Uncontrolled Keywords: | Physical and Theoretical Chemistry, Inorganic Chemistry, Organic Chemistry, Biochemistry, Drug Discovery, Catalysis |
| Language: | German |
| Date: | 1990 |
| Deposited On: | 27 Mar 2014 15:34 |
| Last Modified: | 24 Jan 2022 03:55 |
| Publisher: | Wiley-Blackwell |
| ISSN: | 0018-019X |
| Funders: | Schweizerischer Nationalfonds zur Förderung der wissenschaftlichen Forschung, F. Hoffmann-La Roche AG, Basel, Prof. Hans-E.-Schmid-Stiftung, Anna-Feddersen-Wagner-Fonds |
| OA Status: | Closed |
| Publisher DOI: | https://doi.org/10.1002/hlca.19900730307 |
| Project Information: |
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Ametamey, Simon M